GRAMICIDIN S

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C60H92N12O10
Molecular Weight	1141.4492
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)[C@@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@@H](NC(=O)[C@]4([H])CCCN4C(=O)[C@@H](CC5=CC=CC=C5)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@@H](NC2=O)C(C)C)C(C)C

InChI

InChIKey=IUAYMJGZBVDSGL-XNNAEKOYSA-N

InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C60H92N12O10
Molecular Weight	1141.4492
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://medside.ru/gramitsidin-c

Gramicidin S molecule is amphiphilic, with hydrophobic amino acids (D-Phe, Val, Leu side chains) and charged aminoacid (L-Orn). It exhibits strong antibiotic activity towards Gram-negative and Gram-positive and even several pathogenic fungi. The mode of action is not entirely agreed upon, but it is disruption of the lipid membrane and enhancement of the permeability of the bacterial cytoplasmic membrane. Unfortunately, being hemolytic at even low concentrations, gramicidin S is only used as topical applications at present. Additionally, Gramicidin S has been employed as a spermicide and therapeutic for genital ulcers caused by sexually transmitted disease.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Osteomyelitis 4 Sources: http://medside.ru/gramitsidin-c	Curative	Approved 8583	Gramicidin S Approved Use Unknown
Skin burns 1 Sources: http://medside.ru/gramitsidin-c	Curative	Approved 8583	Gramicidin S Approved Use Unknown
Empyema 2 Sources: http://medside.ru/gramitsidin-c	Curative	Approved 8583	Gramicidin S Approved Use Unknown
Tonsillitis 36 Sources: http://www.rlsnet.ru/mnn_index_id_3322.htm	Curative	Approved 8583	Gramicidin S Approved Use Unknown
Gingivitis 45 Sources: http://www.rlsnet.ru/mnn_index_id_3322.htm	Curative	Approved 8583	Gramicidin S Approved Use Unknown
Stomatitis 7 Sources: http://www.rlsnet.ru/mnn_index_id_3322.htm	Curative	Approved 8583	Gramicidin S Approved Use Unknown

PubMed

Title	Date	PubMed
[Chemical nature of gramicidin C].	1945	20999537
EXPERIMENTAL AND CLINICAL STUDIES ON GRAMICIDIN.	1941-09	16694863

Sample Use Guides

In Vivo Use Guide

Alcoholic preparation solution (2%)

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:02:00 GMT 2025` Edited by `admin` on `Mon Mar 31 19:02:00 GMT 2025`
Record UNII	WHM29QA23F
Record Status	`FAILED`
Record Version

Download

Name

Type

Language

gramicidin s [INN]

Preferred Name

English

GRAMICIDIN S

Official Name

English

CYCLO(L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL)

Common Name

English

Gramicidin s [WHO-DD]

Common Name

English

CYCLO(L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL)

Common Name

English

GRAMICIDIN S 1

Common Name

English

GRAMICIDIN S [MART.]

Common Name

English

GRAMICIDIN C

Common Name

English

GRAMICIDIN S [MI]

Common Name

English

GRAMICIDIN S-A

Common Name

English

GRAMMIDIN

Brand Name

English

Code System Code Type Description

MERCK INDEX

m5837